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• W2891409145 abstract "Iron and N-heterocyclic carbenes (NHCs) have proven to be a successful pair in catalysis, with reactivity and selectivity being highly dependent on the nature of the NHC ligand backbone saturation and N-substituents. Four (NHC)Fe(1,3-dioxan-2-ylethyl)2 complexes have been isolated and spectroscopically characterized to correlate their reactivity to steric effects of the NHC from both the backbone saturation and N-substituents. Only in the extreme case of SIPr where NHC backbone and N-substituent steric effects are the largest is there a major structural perturbation observed crystallographically. The addition of only two hydrogen atoms is sufficient for a drastic change in product selectivity in the coupling of 1-iodo-3-phenylpropane with (2-(1,3-dioxan-2-yl)ethyl)magnesium bromide due to resulting structural perturbations to the precatalyst. Mössbauer spectroscopy and magnetic circular dichroism enabled the correlation of covalency and steric bulk in the SIPr case to its poor selectivity in alkyl–alkyl cross-coupling with iron. Density functional theory calculations provided insight into the electronic structure and molecular orbital effects of ligation changes to the iron center. Finally, charge donation analysis and Mayer bond order calculations further confirmed the stronger Fe–ligand bonding in the SIPr complex. Overall, these studies highlight the importance of considering both N-substituent and backbone steric contributions to structure, bonding, and reactivity in iron-NHCs." @default.
• W2891409145 created "2018-09-27" @default.
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• W2891409145 date "2018-09-06" @default.
• W2891409145 modified "2023-09-30" @default.
• W2891409145 title "Combined Effects of Backbone and N-Substituents on Structure, Bonding, and Reactivity of Alkylated Iron(II)-NHCs" @default.
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• W2891409145 doi "https://doi.org/10.1021/acs.organomet.8b00466" @default.
• W2891409145 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6241324" @default.
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